Monday, October 13

You can pumpkin shake it off at 25 Degrees (736 N. Clark St., River North, 312-943-9700), where, starting today, they’ll be mixing up a milkshake with pumpkin purée sauce, butterscotch, vanilla ice cream, and spiced rum for $10. The boozy treat will be available through the end of October.

Thursday, October 16

Having breakfast for dinner needs no excuse, but if you’re really jonesing for a reason, Floriole Cafe & Bakery (1220 W. Webster Ave., Lincoln Park, 773-883-1313) has you covered. They’re joining forces with Zoe Nathan of the Huckleberry Bakery & Café in Santa Monica and author of the Huckleberry cookbook to prep a version of the mixed-up meal. Tickets are $55 and include a copy of the book (you can also get just dinner for $40)—pick them up here.

Friday, October 17

Trick or treat yourself to pumpkin Frangelico pie ice cream at the one-day-only scoop shop pop-up at David Burke’s Primehouse (616 N. Rush St., River North, 312-660-6000). For $5, you can grab a cone of that or a pecan banana bread flavor—just note that the goodies are available only between 3 and 5 p.m.

Crack open a cold one—a stone crab, that is. Starting at 3 p.m. today, you can get a free claw at Hugo’s Frog Bar & Fish House (1024 N. Rush St., Gold Coast, 312-640-0999) with the purchase of any entrée so staff can get practice opening them up in advance of the start of the crustacean’s season.

Sunday, October 19

What would a week in fall be without multiple opportunities to eat something pumpkin-y? In addition to getting to carve your own gourd in a contest at Antique Taco (1360 N. Milwaukee Ave., Wicker Park, 773-687-8697), the spot will be serving pumpkin beers, pumpkin soup, and pie from Bang Bang Pie Shop. Tickets are $40 for adults and $20 for kids (their tickets don’t include beer, of course) and are available here.